US8580384B2 - Dielectric materials and methods of preparation and use thereof - Google Patents
Dielectric materials and methods of preparation and use thereof Download PDFInfo
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- US8580384B2 US8580384B2 US13/007,148 US201113007148A US8580384B2 US 8580384 B2 US8580384 B2 US 8580384B2 US 201113007148 A US201113007148 A US 201113007148A US 8580384 B2 US8580384 B2 US 8580384B2
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- 239000003989 dielectric material Substances 0.000 title claims description 79
- 238000000034 method Methods 0.000 title description 37
- 229920002521 macromolecule Polymers 0.000 claims abstract description 112
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 54
- 125000000962 organic group Chemical group 0.000 claims abstract description 32
- -1 polysiloxane Polymers 0.000 claims description 161
- 239000004065 semiconductor Substances 0.000 claims description 73
- 239000000412 dendrimer Substances 0.000 claims description 56
- 229920000736 dendritic polymer Polymers 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 229920000587 hyperbranched polymer Polymers 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 239000010409 thin film Substances 0.000 claims description 21
- 125000005647 linker group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 239000003990 capacitor Substances 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 239000004020 conductor Substances 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229920001296 polysiloxane Polymers 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 239000004642 Polyimide Substances 0.000 claims description 10
- 229920001721 polyimide Polymers 0.000 claims description 10
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 9
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 8
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
- TXWRERCHRDBNLG-UHFFFAOYSA-N cubane Chemical compound C12C3C4C1C1C4C3C12 TXWRERCHRDBNLG-UHFFFAOYSA-N 0.000 claims description 2
- XSYZCZPCBXYQTE-UHFFFAOYSA-N cyclodecylcyclodecane Chemical compound C1CCCCCCCCC1C1CCCCCCCCC1 XSYZCZPCBXYQTE-UHFFFAOYSA-N 0.000 claims description 2
- CHVJITGCYZJHLR-UHFFFAOYSA-N cyclohepta-1,3,5-triene Chemical compound C1C=CC=CC=C1 CHVJITGCYZJHLR-UHFFFAOYSA-N 0.000 claims description 2
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 2
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims description 2
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 claims description 2
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical compound C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 claims description 2
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 2
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- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims 1
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- UMHFSEWKWORSLP-UHFFFAOYSA-N thiophene 1,1-dioxide Chemical compound O=S1(=O)C=CC=C1 UMHFSEWKWORSLP-UHFFFAOYSA-N 0.000 description 1
- LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical compound O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N trimethylmethane Natural products CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
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- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
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- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/307—Other macromolecular compounds
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- C08G63/912—Polymers modified by chemical after-treatment derived from hydroxycarboxylic acids
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- H01L29/40—Electrodes ; Multistep manufacturing processes therefor
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- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/464—Lateral top-gate IGFETs comprising only a single gate
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Definitions
- TFTs thin-film transistors
- organic or hybrid semiconductor and dielectric materials printable conductors, flexible substrates, and low-cost (e.g., large-area and low-temperature) manufacturing processes.
- TFTs are key building blocks of any electronic circuit.
- a critical component in most solution-processed TFTs is the dielectric layer, which serves as the gate electrical insulator material.
- the dielectric layer can be formed on either the gate contact (in bottom-gate transistor structures) or on the semiconductor layer (in top-gate transistor structures) by depositing an electrically insulating (i.e., dielectric) compound using, for example, a solution-phase process such as spin-coating or printing.
- the solvent mobilizing the dielectric compound does not dissolve the semiconductor material and vice versa. Because semiconductor materials are usually soluble in organic chlorinated polar solvents, it is important that the dielectric material affording the dielectric layer is processable in other types of organic solvents. Furthermore, to reduce leakage current density, maximize gate capacitance, and enable large-quantity charge carrier accumulation in the semiconductor layer upon application of an electrical potential on the gate electrode, it is desirable that the dielectric constant (k, a property also known as relative permittivity) of the gate dielectric is sufficiently large.
- a low-k polymeric material that can be used as the gate dielectric is CYTOP®, a fluorinated polymer (k ⁇ 2), whereas poly(methyl methacrylate) (k ⁇ 3.6) and poly(vinyl phenol) (k ⁇ 4.5-5.5) are examples of high-k polymeric materials.
- CYTOP® a fluorinated polymer
- k ⁇ 2 a fluorinated polymer
- k ⁇ 3.6 poly(methyl methacrylate)
- poly(vinyl phenol) k ⁇ 4.5-5.5
- the present teachings provide electrically insulating (i.e., dielectric) dendritic macromolecules, dendritic macromolecule-based dielectric compositions (e.g., formulations) and materials (e.g., films), and associated devices that can address various deficiencies and shortcomings of the prior art, including those outlined above.
- dendritic macromolecules have been used as porogens with other polymers to prepare low-k nanoporous dielectric materials
- the dendritic macromolecules typically are incorporated into a precursor form of the material as fugitives only, and are subsequently decomposed (usually via thermal treatment) to create empty (air-filled), low-k voids (k of air is about 1). Therefore, the dendritic macromolecules are not present in the final dielectric material.
- dendritic macromolecules that can enable high-k dielectric materials and at the same time withstand relatively high-temperature processing and have good solubility in organic solvents orthogonal to common solvents used to process organic semiconductors are unknown.
- the present teachings provide various dendritic macromolecules that can be used to prepare dielectric materials.
- the dendritic macromolecules of the present teachings are end-functionalized with organic groups that include at least one cyclic groups.
- the present dendritic macromolecules can include a dendritic or hyperbranched core (which includes the initiator core and generations of branches) that is characterized by a high dielectric constant (e.g., k>3).
- the dendritic or hyperbranched core can be a polymer other than a polysiloxane.
- the dendritic or hyperbranched core can include at least one non-aromatic repeating units; that is, at least one of the repeating units from which the branches are derived does not include any aromatic groups.
- the dendritic or hyperbranched core can consist of non-aromatic branches; that is, the various generations of branches are derived from non-aromatic repeating units only, although as described hereinbelow, the end groups of the branches (i.e., the periphery of the dendritic macromolecules) can include one or more aromatic groups.
- the present dendritic macromolecules can include branched ends that are functionalized with an organic group that includes one, two, three, or four optionally substituted 3-40 membered cyclic groups.
- each of the optionally substituted 3-40 membered cyclic groups independently can be selected from an optionally substituted C 3-40 cycloalkyl group, an optionally substituted C 6-40 aryl group, an optionally substituted 3-40 membered cycloheteroalkyl group, and an optionally substituted 5-40 membered heteroaryl group.
- the organic group can include at least one optionally substituted C 3-40 cycloalkyl group.
- the organic group can include at least one optionally substituted C 6-40 aryl group.
- the cyclic groups can be covalently bonded to each other (directly or via a linker group).
- the two or more cyclic groups can be bonded to a common atom.
- the common atom can be a carbon (C) atom or a heteroatom such as nitrogen (N) or phosphorus (P), where P can be oxidized.
- the organic end group includes three or four cyclic groups, one of the cyclic groups can serve as a linker group.
- the organic end group can be crosslinkable, e.g., photocrosslinkable or thermally crosslinkable at temperatures which do not decompose the dendrimer core.
- the photo/thermally crosslinkable end group can include a photo/thermally crosslinkable linker, a photo/thermally crosslinkable cyclic group, a cyclic group that is substituted with one or more photo/thermally crosslinkable groups, or combinations thereof.
- a cyclic group can be photocrosslinkable because of the presence of one or more unsaturated bonds within the ring.
- a cyclic group can be thermally crosslinkable because of the presence of thermally labile groups within the ring.
- Examples of a photocrosslinkable organic end group include an organic end group comprising a cinnamoyl group or a coumarinyl group.
- compositions for forming dielectric materials where the compositions include one or more dendritic macromolecules dissolved or dispersed in a liquid medium.
- the compositions can be used to prepare dielectric materials using various solution processes, including various printing techniques.
- the present teachings further provide electronic devices that include the dielectric materials described herein.
- electronic devices include, but are not limited to, thin-film transistors (TFTs) (e.g., field-effect transistors (FETs)) and thin-film capacitors.
- TFTs thin-film transistors
- FETs field-effect transistors
- these devices also can include at least a semiconductor component and/or one or more electrically conductive components.
- the present teachings can provide a thin-film transistor device including a dielectric thin-film layer and a semiconductor thin-film layer, wherein the dielectric thin-film layer is coupled to the semiconductor thin-film layer on one side and an electrically conductive component (i.e., a gate electrode) on the opposite side. Additional electrically conductive components (i.e., a source electrode and a drain electrode) can be present and coupled to the semiconductor thin-film layer on an opposite side to the dielectric thin-film layer.
- TFTs thin-film transistors
- FETs field-effect transistors
- FIG. 1 shows the chemical structure of a fourth-generation hyperbranched polyester based on bis-hydroxymethyl propionic acid (bis-MPA) repeating units having 64 hydroxyl groups (Hyperbranched Bis-MPA Polyester-64-Hydroxyl, Generation 4, available from Sigma-Aldrich Corporation, St. Louis, Mo.).
- bis-MPA bis-hydroxymethyl propionic acid
- FIG. 2 shows a representative 1 H NMR spectrum (in DMSO-d 6 ) of Hyperbranched Bis-MPA Polyester-64-Hydroxyl, Generation 4.
- FIG. 3 shows a representative 13 C NMR spectrum (in DMSO-d 6 ) of Hyperbranched Bis-MPA Polyester-64-Hydroxyl, Generation 4.
- FIG. 4 shows a representative 1 H NMR spectrum (in CDCl 3 ) of polymer D1.
- FIG. 5 shows a representative 1 H NMR spectrum (in CDCl 3 ) of polymer D2.
- FIG. 6 shows a representative 13 C NMR spectrum (in CDCl 3 ) of polymer D2.
- FIG. 7 shows a representative 1 H NMR spectrum (in CDCl 3 ) of polymer D6.
- FIG. 8 shows DSC plots of polymers D2 (C), D1 (D), D4 (E), D7 (F), and D8 (G) according to the present teachings as compared to the unfunctionalized hyperbranched bis-MPA polymer (B).
- FIG. 9 illustrates four different configurations of thin film transistors: a) bottom-gate top contact, b) bottom-gate bottom-contact, c) top-gate bottom-contact, and d) top-gate top-contact; each of which can be used to incorporate one or more dendritic macromolecules of the present teachings, particularly as the dielectric layer or part of the dielectric component.
- FIG. 10 illustrates representative dielectric constant (k) vs. voltage (V) and capacitance (C) vs. frequency (f) plots of a dendrimer-based capacitor according to the present teachings and a comparative capacitor incorporating a conventional dielectric material (PMMA).
- FIG. 11 provides a leakage current density (J) vs. voltage (V) plot of metal-insulator-metal capacitor structures that were fabricated using dielectric materials of the present teachings.
- FIG. 12 provides representative output plots of top-gate dicyano-perylenecarboxydiimide-based organic field effect transistors fabricated with dielectric materials of the present teachings.
- FIG. 13 provides a representative output plot of a bottom-gate pentacene-based organic field effect transistor fabricated with a dielectric material of the present teachings.
- the present teachings relate to organic dielectric materials prepared from end-functionalized dendritic macromolecules, compositions (formulations) for forming these dielectric materials, and composites and devices that include such dielectric materials.
- the present teachings provide dendritic macromolecules that can be soluble in organic solvents that are orthogonal to those used to process common organic semiconductor materials, and can exhibit a high dielectric constant (k) and a low leakage current density when used as an electrically insulating (dielectric) material.
- the dielectric materials also can be air-stable and can have long shelf stability, and can be compatible with a wide range of p-type and n-type organic and inorganic semiconductors, making them attractive materials for fabricating various electronic devices.
- compositions are described as having, including, or comprising specific components, or where processes are described as having, including, or comprising specific process steps, it is contemplated that compositions of the present teachings also consist essentially of, or consist of, the recited components, and that the processes of the present teachings also consist essentially of, or consist of, the recited process steps.
- halo or “halogen” refers to fluoro, chloro, bromo, and iodo.
- oxo refers to a double-bonded oxygen (i.e., ⁇ O).
- alkyl refers to a straight-chain or branched saturated hydrocarbon group.
- alkyl groups include methyl (Me), ethyl (Et), propyl (e.g., n-propyl and iso-propyl), butyl (e.g., n-butyl, iso-butyl, sec-butyl, tert-butyl), pentyl groups (e.g., n-pentyl, iso-pentyl, neopentyl), hexyl groups, and the like.
- an alkyl group can have 1 to 40 carbon atoms (i.e., C 1-40 alkyl group), for example, 1-20 carbon atoms (i.e., C 1-20 alkyl group).
- an alkyl group can have 1 to 6 carbon atoms, and can be referred to as a “lower alkyl group.” Examples of lower alkyl groups include methyl, ethyl, propyl (e.g., n-propyl and iso-propyl), butyl (e.g., n-butyl, iso-butyl, sec-butyl, tert-butyl), and hexyl groups.
- alkyl groups can be substituted as described herein. An alkyl group is generally not substituted with another alkyl group, an alkenyl group, or an alkynyl group.
- haloalkyl refers to an alkyl group having one or more halogen substituents.
- a haloalkyl group can have 1 to 40 carbon atoms (i.e., C 1-40 haloalkyl group), for example, 1 to 20 carbon atoms (i.e., C 1-20 haloalkyl group).
- Examples of haloalkyl groups include CF 3 , C 2 F 5 , CHF 2 , CH 2 F, CCl 3 , CHCl 2 , CH 2 Cl, C 2 Cl 5 , and the like.
- Perhaloalkyl groups i.e., alkyl groups where all of the hydrogen atoms are replaced with halogen atoms (e.g., CF 3 and C 2 F 5 ), are included within the definition of “haloalkyl.”
- a C 1-40 haloalkyl group can have the formula —C z H 2z+1 ⁇ t X 0 t , where X 0 , at each occurrence, is F, Cl, Br or I, z is an integer in the range of 1 to 40, and t is an integer in the range of 1 to 81, provided that t is less than or equal to 2z+1.
- Haloalkyl groups that are not perhaloalkyl groups can be substituted as described herein.
- alkoxy refers to —O-alkyl group.
- alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy (e.g., n-propoxy and isopropoxy), t-butoxy, pentoxyl, hexoxyl groups, and the like.
- the alkyl group in the —O-alkyl group can be substituted as described herein.
- alkylthio refers to an —S-alkyl group.
- alkylthio groups include, but are not limited to, methylthio, ethylthio, propylthio (e.g., n-propylthio and isopropylthio), t-butylthio, pentylthio, hexylthio groups, and the like.
- the alkyl group in the —S-alkyl group can be substituted as described herein.
- alkenyl refers to a straight-chain or branched alkyl group having one or more carbon-carbon double bonds.
- alkenyl groups include ethenyl, propenyl, butenyl, pentenyl, hexenyl, butadienyl, pentadienyl, hexadienyl groups, and the like.
- the one or more carbon-carbon double bonds can be internal (such as in 2-butene) or terminal (such as in 1-butene).
- an alkenyl group can have 2 to 40 carbon atoms (i.e., C 2-40 alkenyl group), for example, 2 to 20 carbon atoms (i.e., C 2-20 alkenyl group).
- alkenyl groups can be substituted as described herein.
- An alkenyl group is generally not substituted with another alkenyl group, an alkyl group, or an alkynyl group.
- alkynyl refers to a straight-chain or branched alkyl group having one or more triple carbon-carbon bonds.
- alkynyl groups include ethynyl, propynyl, butynyl, pentynyl, hexynyl, and the like.
- the one or more triple carbon-carbon bonds can be internal (such as in 2-butyne) or terminal (such as in 1-butyne).
- an alkynyl group can have 2 to 40 carbon atoms (i.e., C 2-40 alkynyl group), for example, 2 to 20 carbon atoms (i.e., C 2-20 alkynyl group).
- alkynyl groups can be substituted as described herein.
- An alkynyl group is generally not substituted with another alkynyl group, an alkyl group, or an alkenyl group.
- cyclic refers to an organic closed-ring group including cycloalkyl groups, aryl groups, cycloheteroalkyl groups, and heteroaryl groups as defined herein.
- cycloalkyl refers to a non-aromatic carbocyclic group including cyclized alkyl, cyclized alkenyl, and cyclized alkynyl groups.
- a cycloalkyl group can have 3 to 40 carbon atoms (i.e., C 3-40 cycloalkyl group), for example, 3 to 20 carbon atoms.
- a cycloalkyl group can be monocyclic (e.g., cyclohexyl) or polycyclic (e.g., containing fused, bridged, and/or spiro ring systems), where the carbon atoms are located inside the ring system.
- cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cyclohexadienyl, cycloheptatrienyl, norbornyl, norpinyl, norcaryl, adamantyl, and spiro[4.5]decanyl groups, as well as their homologs, isomers, and the like.
- cycloalkyl groups can be substituted as described herein.
- heteroatom refers to an atom of any element other than carbon or hydrogen and includes, for example, nitrogen, oxygen, silicon, sulfur, phosphorus, and selenium.
- cycloheteroalkyl refers to a non-aromatic cycloalkyl group that contains at least one ring heteroatom selected from O, S, Se, N, P, and Si (e.g., O, S, and N), and optionally contains one or more double or triple bonds.
- a cycloheteroalkyl group can have 3 to 40 ring atoms (i.e., 3-40 membered cycloheteroalkyl group), for example, 3 to 20 ring atoms.
- N, P, S, or Se atoms in a cycloheteroalkyl ring may be oxidized (e.g., morpholine N-oxide, thiomorpholine S-oxide, thiomorpholine S,S-dioxide).
- nitrogen or phosphorus atoms of cycloheteroalkyl groups can bear a substituent, for example, a hydrogen atom, an alkyl group, or other substituents as described herein.
- Cycloheteroalkyl groups can also contain one or more oxo groups, such as oxopiperidyl, oxooxazolidyl, dioxo-(1H,3H)-pyrimidyl, oxo-2(1H)-pyridyl, and the like.
- oxo groups such as oxopiperidyl, oxooxazolidyl, dioxo-(1H,3H)-pyrimidyl, oxo-2(1H)-pyridyl, and the like.
- cycloheteroalkyl groups include, among others, morpholinyl, thiomorpholinyl, pyranyl, imidazolidinyl, imidazolinyl, oxazolidinyl, pyrazolidinyl, pyrazolinyl, pyrrolidinyl, pyrrolinyl, tetrahydrofuranyl, tetrahydrothiophenyl, piperidinyl, piperazinyl, and the like.
- cycloheteroalkyl groups can be substituted as described herein.
- aryl refers to an aromatic monocyclic hydrocarbon ring system or a polycyclic ring system in which two or more aromatic hydrocarbon rings are fused (i.e., having a bond in common with) together or at least one aromatic monocyclic hydrocarbon ring is fused to one or more cycloalkyl and/or cycloheteroalkyl rings.
- An aryl group can have 6 to 40 carbon atoms in its ring system, which can include multiple fused rings.
- a polycyclic aryl group can have from 8 to 40 carbon atoms. Any suitable ring position of the aryl group can be covalently linked to the defined chemical structure.
- aryl groups having only aromatic carbocyclic ring(s) include phenyl, 1-naphthyl (bicyclic), 2-naphthyl (bicyclic), anthracenyl (tricyclic), phenanthrenyl (tricyclic), and like groups.
- polycyclic ring systems in which at least one aromatic carbocyclic ring is fused to one or more cycloalkyl and/or cycloheteroalkyl rings include, among others, benzo derivatives of cyclopentane (i.e., an indanyl group, which is a 5,6-bicyclic cycloalkyl/aromatic ring system), cyclohexane (i.e., a tetrahydronaphthyl group, which is a 6,6-bicyclic cycloalkyl/aromatic ring system), imidazoline (i.e., a benzimidazolinyl group, which is a 5,6-bicyclic cycloheteroalkyl/aromatic ring system), and pyran (i.e., a chromenyl group, which is a 6,6-bicyclic cycloheteroalkyl/aromatic ring system).
- aryl groups include benzodioxanyl, benzodioxolyl, chromanyl, indolinyl groups, and the like.
- aryl groups can be substituted as described herein.
- an aryl group can have one or more halogen substituents, and can be referred to as a “haloaryl” group.
- Perhaloaryl groups i.e., aryl groups where all of the hydrogen atoms are replaced with halogen atoms (e.g., —C 6 F 5 ), are included within the definition of “haloaryl.”
- an aryl group is substituted with another aryl group and can be referred to as a biaryl group.
- Each of the aryl groups in the biaryl group can be substituted as disclosed herein.
- heteroaryl refers to an aromatic monocyclic ring system containing at least one ring heteroatom selected from oxygen (O), nitrogen (N), sulfur (S), silicon (Si), and selenium (Se) or a polycyclic ring system where at least one of the rings present in the ring system is aromatic and contains at least one ring heteroatom.
- Polycyclic heteroaryl groups include two or more heteroaryl rings fused together and monocyclic heteroaryl rings fused to one or more aromatic carbocyclic rings, non-aromatic carbocyclic rings, and/or non-aromatic cycloheteroalkyl rings.
- a heteroaryl group as a whole, can have, for example, 5 to 40 ring atoms and contain 1-5 ring heteroatoms.
- the heteroaryl group can be attached to the defined chemical structure at any heteroatom or carbon atom that results in a stable structure.
- heteroaryl rings do not contain O—O, S—S, or S—O bonds.
- one or more N or S atoms in a heteroaryl group can be oxidized (e.g., pyridine N-oxide, thiophene S-oxide, thiophene S,S-dioxide).
- heteroaryl groups include, for example, the 5- or 6-membered monocyclic and 5-6 bicyclic ring systems shown below:
- T is O, S, NH, N-alkyl, N-aryl, N-(arylalkyl) (e.g., N-benzyl), SiH 2 , SiH(alkyl), Si(alkyl) 2 , SiH(arylalkyl), Si(arylalkyl) 2 , or Si(alkyl)(arylalkyl).
- N-alkyl N-aryl, N-(arylalkyl) (e.g., N-benzyl)
- SiH 2 SiH(alkyl), Si(alkyl) 2 , SiH(arylalkyl), Si(arylalkyl) 2 , or Si(alkyl)(arylalkyl).
- heteroaryl rings examples include pyrrolyl, furyl, thienyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazolyl, tetrazolyl, pyrazolyl, imidazolyl, isothiazolyl, thiazolyl, thiadiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, indolyl, isoindolyl, benzofuryl, benzothienyl, quinolyl, 2-methylquinolyl, isoquinolyl, quinoxalyl, quinazolyl, benzotriazolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxadiazolyl, benzoxazolyl, cinnolinyl, 1H-indazolyl, 2H-indazolyl
- heteroaryl groups include 4,5,6,7-tetrahydroindolyl, tetrahydroquinolinyl, benzothienopyridinyl, benzofuropyridinyl groups, and the like. In some embodiments, heteroaryl groups can be substituted as described herein.
- Compounds of the present teachings can include a “multivalent group” defined herein as a linking group capable of forming a covalent bond with multiple moieties.
- a divalent group can form a covalent bond with two moieties
- a trivalent group can form a covalent bond with three moieties
- a tetravalent group can form a covalent bond with four moieties.
- C 1-6 alkyl is specifically intended to individually disclose C 1 , C 2 , C 3 , C 4 , C 5 , C 6 , C 1 -C 6 , C 1 -C 5 , C 1 -C 4 , C 1 -C 3 , C 1 -C 2 , C 2 -C 6 , C 2 -C 5 , C 2 -C 4 , C 2 -C 3 , C 3 -C 6 , C 3 -C 5 , C 3 -C 4 , C 4 -C 6 , C 4 -C 5 , and C 5 -C 6 alkyl.
- an integer in the range of 0 to 40 is specifically intended to individually disclose 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, and 40, and an integer in the range of 1 to 20 is specifically intended to individually disclose 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20.
- phrases “optionally substituted with 1-5 substituents” is specifically intended to individually disclose a chemical group that can include 0, 1, 2, 3, 4, 5, 0-5, 0-4, 0-3, 0-2, 0-1, 1-5, 1-4, 1-3, 1-2, 2-5, 2-4, 2-3, 3-5, 3-4, and 4-5 substituents.
- a “p-type semiconductor material” or a “p-type semiconductor” refers to a semiconductor material having holes as the majority current carriers.
- a p-type semiconductor material when deposited on a substrate, it can provide a hole mobility in excess of about 10 ⁇ 5 cm 2 /Vs.
- a p-type semiconductor in the case of field-effect devices, can also exhibit a current on/off ratio of greater than about 10.
- an “n-type semiconductor material” or an “n-type semiconductor” refers to a semiconductor material having electrons as the majority current carriers.
- an n-type semiconductor material when deposited on a substrate, it can provide an electron mobility in excess of about 10 ⁇ 5 cm 2 /Vs.
- an n-type semiconductor can also exhibit a current on/off ratio of greater than about 10.
- a “dielectric material” has a conductivity in the order of 10 ⁇ 6 Scm ⁇ 1 or less to avoid current leakage to an adjacent electrical conductor.
- the two components can be directly in contact (e.g., directly coupled to each other), or the two components can be coupled to each other via one or more intervening components or layers.
- the present teachings provide dendritic macromolecules having end groups that include at least one cyclic group.
- the dendritic macromolecules have branched ends that are functionalized with organic groups that include one or more cyclic groups.
- the cyclic group can be monocyclic or polycyclic (fused, spiro, or bridged), can be carbocyclic or include one or more heteroatoms, can be completely saturated or include one or more unsaturated bonds, and can be unsubstituted or substituted with one or more functional groups.
- dendritic macromolecule refers to dendrimers, hyperbranched polymers (HBPs), and other repeated branched polymers such as star-shaped and star-branched polymers.
- the basic structure of a dendritic macromolecule includes a multivalent initiator core and a plurality of generations of branches extending from the core, which leads to a compact globular or quasi-globular structure with a large number of end groups per molecule. The number of branch points increases upon moving from the initiator core towards the end groups and defines generations.
- generations encompasses pseudo-generations, in particular, when used in the context of hyperbranched polymers.
- Dendrimers typically are prepared via stepwise synthesis, which gives rise to a highly regular branching pattern, a definite molecular weight, a low polydispersity index and a well-defined number of end groups.
- the synthesis of hyperbranched polymers can be less strictly controlled, and many hyperbranched polymers can be prepared using a one-pot process, which make them preferable to dendrimers in many applications.
- hyperbranched polymers While hyperbranched polymers have irregular branches and a broader molecular weight distribution, they do conserve the essential features of dendrimers, namely a high degree of end-group functionality and a globular architecture.
- dendritic macromolecules also can have interior functionalities.
- dendritic macromolecules such as dendrimers and hyperbranched polymers can have an average of at least 16 end groups per molecule for second-generation materials (the branches immediately attached to the initiator core are considered zero-generation), increasing by a factor of at least 2 for each successive generation.
- Number average molar masses of second-generation dendrimers or hyperbranched polymers usually are greater than about 1500 g/mol, and the molar masses increase exponentially per generation, reaching about 8000 g/mol for a fourth-generation polymer.
- the molecular weight of a dendritic macromolecule can be about 100 g/mol per end group, although this will vary according to the exact formulation.
- the present dendritic macromolecules can have two, three, four, five, six, seven or more generations, and the number of end groups per dendritic macromolecule can range from 12 to about 1,000.
- dendritic macromolecules can be characterized by unusual properties such as (1) less flexibility/molecular fragment motion, (2) lower entanglement degree, and, very relevant to the materials disclosed herein, (3) a significant chain-end effect.
- the present dendritic macromolecule can be a dendrimer or hyperbranched polymer including a polymerized product of one or more repeating units which, upon conventional (i.e., linear) polymerization can provide a dielectric polymer associated with a high dielectric constant, i.e., a dielectric constant of at least 2.5, preferably larger than 3.
- the monomers of polyacrylates such as poly(methyl methacrylate) (PMMA); polyolefins such as poly(vinyl phenol) (PVP), poly(vinyl chloride) (PVC), poly(vinyl alcohol) (PVA), and poly(vinylidene fluoride) (PVDF); cyanated polysaccharides such as polycyanopullulan, poly(cyanoethylated pullulan), cyanoethylated cellulose, and cyanated poly(vinyl alcohol); polysiloxanes; polyimides such as polymaleimides; aliphatic polyethers such as poly(ethylene glycol) and polypropylene glycol); polyesters such as poly(ethylene terephthalate); polyamines; polyamides; polyimines; polyurethanes; and combinations thereof can be included as repeating units in the present dendritic macromolecules.
- the present dendritic macromolecules can be a dendrimer or hyperbranched
- the branching of the present dendritic macromolecules is enabled by multifunctional monomers, which serve as branching agents and provide the branch points in the dendritic macromolecules.
- the branching agents can include three or more functional groups independently selected from hydroxyl groups, amino groups, vinyl groups, alkynyl groups, azido groups, thiol groups, epoxy groups, carboxylic acid groups including acyl halides and anhydrides, and combinations thereof.
- the initiator can be a multivalent compound having multiple hydroxyl groups such as:
- the initiator can have multiple amine groups and/or carboxylic acid groups.
- the initiator can be:
- polymerization chemistry can be used to prepare the present dendritic macromolecules, including condensation, anionic additional polymerization, controlled free radical polymerization (e.g., atom transfer radical polymerization), and controlled ring opening reactions.
- hyperbranched polyesters and copolymers thereof can be prepared by condensation of one or more self-condensable monomers, where the monomers can have one hydroxyl group and two or three carboxylic acid groups, or one carboxylic acid group and two or three hydroxyl groups.
- One common example of such a self-condensable monomer is bis-hydroxymethyl propionic acid (bis-MPA or dimethylolpropionic acid (DMPA)).
- Hyperbranched polyesters also can be obtained by controlled ring opening of cyclic precursors such as lactones and lactides, or polymerization of multifunctional vinyl ester derivatives.
- the present dendritic macromolecule can be a dendrimer or hyperbranched polymer other than a polysiloxane dendrimer or a hyperbranched polysiloxane.
- the present dendritic macromolecule can be selected from polyester, polyamide, polyether, polyamine, polyurethane, polyolefin, polyimide, polycarbosilane, and copolymers thereof.
- the present dendritic macromolecule can be a non-silicon-based polymer.
- the present dendritic macromolecule can be a dendrimer or hyperbranched polymer selected from poly(amido-amine), poly(amide-ester), poly(amine-ester), and poly(ether-ester).
- the repeating units in the dendritic macromolecule can include aliphatic and/or aromatic groups.
- the present dendritic macromolecule can include at least one non-aromatic repeating unit.
- the present dendritic macromolecule can include both aliphatic and aromatic repeating units.
- the present dendritic macromolecule can include only non-aromatic repeating units.
- the present dendritic macromolecule can be a hyperbranched polyester or poly(ether-ester) derived from an initiator having three or more hydroxyl groups.
- the present dendritic macromolecule can be derived from a pentaerythritol core:
- dendritic macromolecules include poly(amidoamine) (PAMAM) dendrimers or hyperbranched polymers, poly(propylene-imine) dendrimers or hyperbranched polymers, and poly(amide-ester) dendrimers or hyperbranched polymers such as those described in International Publication No. WO 2009/136853, the entire disclosure of which is incorporated by reference herein.
- PAMAM poly(amidoamine)
- PAMAM poly(amidoamine) dendrimers or hyperbranched polymers
- poly(propylene-imine) dendrimers or hyperbranched polymers poly(amide-ester) dendrimers or hyperbranched polymers
- amide-ester dendrimers or hyperbranched polymers such as those described in International Publication No. WO 2009/136853, the entire disclosure of which is incorporated by reference herein.
- dendritic macromolecules that can be functionalized according to the present teachings include
- the present dendritic macromolecules have branched ends that are functionalized with organic groups that include one or more cyclic groups.
- each of the end groups can include one, two, three or four optionally substituted cyclic groups.
- the cyclic groups can be covalently bonded to each other directly or via a linker group, or the cyclic groups can be attached to a common atom directly or via a linker group.
- one of the cyclic groups can function as a linker group.
- each cyclic group can be monocyclic or polycyclic.
- Polycyclic groups can have 2-10 rings where the rings are fused or connected by one or more spiro atoms or bridged groups.
- Each cyclic group can be carbocyclic or can include one or more heteroatoms (e.g., O, S, and/or N). Also, each cyclic group can be completely saturated or include one or more unsaturated (double or triple) bonds. In addition, each cyclic group can be unsubstituted or substituted with one or more functional groups.
- heteroatoms e.g., O, S, and/or N
- each cyclic group can be completely saturated or include one or more unsaturated (double or triple) bonds.
- each cyclic group can be unsubstituted or substituted with one or more functional groups.
- the present dendritic macromolecules have branched ends that are functionalized with organic groups that include one, two, three, or four optionally substituted 3-40 membered cyclic groups.
- the organic group as a whole can have 3-100 carbon atoms.
- Each cyclic group optionally can be substituted with 1-5 substituents, where the optional substituents independently can be selected from halogens (e.g., Cl, F), CN, OH, C 1-10 alkyl groups, C 2-10 alkenyl groups, C 2-10 alkynyl groups, C 1-10 haloalkyl groups, C 1-10 alkoxyl groups, and C 1-10 alkylthio groups.
- the organic group can be entirely non-aromatic, that is, the organic group does not include any aryl or heteroaryl groups.
- each of the cyclic groups in the organic group can be an optionally substituted C 3-40 cycloalkyl group.
- the organic group can include one, two, three or four C 3-40 cycloalkyl groups, each of which optionally can be substituted with 1-5 C 1-10 alkyl groups and/or C 2-10 alkenyl groups.
- Illustrative cycloalkyl moieties include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, bicyclobutane, bicyclopentane, bicyclohexane (e.g., norbornane, norpinane, norcarane), bicycloheptane, bicyclooctane, bicyclononane, bicyclodecane, bicycloundecane, various steranes, and cage compounds such as adamantane, cubane, and prismane.
- cycloalkyl moieties include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, bicyclobutane, bicyclopentane, bicyclohexane (e.g., norbornane, norpinane, norcarane), bicycloh
- cycloalkyl moieties and cycloalkyl moieties that include at least one unsaturated bond include cyclopentene, cyclohexene, cyclohexadiene, cycloheptatriene, norbornene, and completely or partially hydrogenated analogs of toluene, xylene, naphthalene, anthracene, phenanthrene, cyclopentaphenanthrene, pyrene, benzopyrene, chrysene, naphthacene, pentacene, pentalene, fluoranthene, benzofluoranthene, fluorene, benzofluorene, perylene, picene, coronene, corannulene, triphenylene, and ovalene.
- the cycloalkyl moieties can be partially fluorinated or perfluorinated.
- the organic group can include two or more cyclic groups which are covalently bonded to each other directly or via a linker group. In some embodiments, the organic group can include two or more cyclic groups which are attached to a common atom directly or via a linker group. The common atom typically is carbon, but in some embodiments, two or more cyclic groups can be attached to a common heteroatom such as N or P which optionally can be oxidized. In certain embodiments, the organic group can include a cyclic group substituted with two or three cyclic groups.
- non-aromatic end groups examples include:
- organic groups having two cycloalkyl moieties attached to a common heteroatom include:
- the present dendritic macromolecules have branched ends that are functionalized with a crosslinkable organic group, for example, a photo- and/or thermally crosslinkable organic group, where the organic group includes one, two, three, or four optionally substituted 3-40 membered cyclic groups as described above.
- a crosslinkable organic group for example, a photo- and/or thermally crosslinkable organic group, where the organic group includes one, two, three, or four optionally substituted 3-40 membered cyclic groups as described above.
- one or more cyclic groups in the crosslinkable organic group can be photo- and/or thermally crosslinkable.
- a cyclic group can be photocrosslinkable because of the presence of one or more unsaturated bonds within the ring.
- a cyclic group can be thermally crosslinkable because of the presence of thermally labile groups within the ring.
- the crosslinkable organic group can include a photo/thermally crosslinkable linker, a photo/thermally crosslinkable cyclic group, a cyclic group that is substituted with one or more photo/thermally crosslinkable groups, or combinations thereof.
- photocrosslinkable substituents include C 2-10 alkenyl groups, C 2-10 alkynyl groups, and azido groups.
- photocrosslinkable linkers include divalent C 2-10 alkenyl groups, divalent C 2-10 alkynyl groups, and azido linker groups.
- the photocrosslinking chemistry can involve a 2+2 photo-stimulated cycloaddition that provides stable cyclobutane moieties.
- the photocrosslinking chemistry also can involve free radical additions affording C—C and C—O bonds.
- Dendritic macromolecules according to these embodiments can be cured by exposure to ultraviolet light, for example, at a wavelength of about 250-500 nm (e.g., between about 300 nm and about 450 nm).
- Photocrosslinking also can be achieved by other types of radiation, for example, with ion beams of charged particles, and electron beams with radioactive sources.
- photocrosslinkable end groups examples include:
- the one or more cyclic groups can be thermally crosslinkable.
- the thermal crosslinking can be initiated by high temperature or by radical initiators such as azobisisobutyronitrile (AIBN), photoacid generators such as triphenylsulfonium triflate, radical photoinitiators such as diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO), or photosensitizers such as benzophenone.
- the thermally-induced process should occur at a low temperature, typically lower than about 300° C. but preferably lower than about 200° C., to avoid chemical decomposition of the dendrimer core.
- Dendritic macromolecules according to these embodiments can be cured at a temperature below about 300° C., and in certain embodiments, as low as about 120° C., according to the chemistries of the employed groups.
- thermally crosslinkable end groups examples include:
- dendritic macromolecules according to the present teachings can be described by the formula: D-(L-R 1 ) n wherein: D is the residue of a dendrimer or hyperbranched polymer; L is a covalent bond or a linker group; R 1 is an organic group comprising one, two, three or four 3-40 membered optionally substituted cyclic groups; and n is an integer in the range of 12-1024.
- D can be the residue of a dendrimer or hyperbranched polymer other than a polysiloxane dendrimer or a hyperbranched polysiloxane. In various embodiments, D can be the residue of a dendrimer or hyperbranched polymer including at least one non-aromatic repeating units. In certain embodiments, D can be the residue of an aliphatic-aromatic dendrimer or an aliphatic-aromatic hyperbranched polymer. In particular embodiments, D can be the residue of an aliphatic dendrimer or an aliphatic hyperbranched polymer.
- D can be the residue of a dendrimer or hyperbranched polymer selected from an aliphatic polyester, an aliphatic-aromatic polyester, an aliphatic polyamide, an aliphatic-aromatic polyamide, an aliphatic polyether, an aliphatic-aromatic polyether, an aliphatic polyamine, an aliphatic-aromatic polyamine, an aliphatic polyurethane, an aliphatic-aromatic polyurethane, an aliphatic polyolefin, an aliphatic-aromatic polyolefin, an aliphatic polyimide, an aliphatic-aromatic polyimide, and copolymers thereof.
- a dendrimer or hyperbranched polymer selected from an aliphatic polyester, an aliphatic-aromatic polyester, an aliphatic polyamide, an aliphatic-aromatic polyamide, an aliphatic polyether, an aliphatic-aromatic polyether, an ali
- the present dendritic macromolecules can be obtained by reacting a hyperbranched polymer or a dendrimer including initial end groups (referred herein as first reactive groups) that are reactive to a compound of the formula X—R 1 , where X is a second reactive group that can react with a first reactive group to provide a covalent bond or a linker group such as —O—, —C(O)—, —OC(O)—, —NR—, —NRC(O)—, —O—SiR 2 —, -Ph-, -Ph-O—, -PhCH 2 —, -PhCH 2 —O—, -1,2,3-triazolo-, —RC ⁇ CR—, —C ⁇ C—, —SO 2 —, and —S(O)—, where R is H or a C 1-6 alkyl group, Ph is a divalent phenyl group, and R 1 is the chemical group comprising one or more
- the functionalization of the dendritic macromolecule with R 1 can be carried out using various chemistries known in the art including substitution reactions such as esterification (reaction between a hydroxyl group and a carboxylic acid derivative to provide an ester linker group), additional reactions including click chemistry (e.g., cycloaddition between an azide and an alkyne to provide a 1,2,3-triazolo-linker group), and so forth.
- substitution reactions such as esterification (reaction between a hydroxyl group and a carboxylic acid derivative to provide an ester linker group), additional reactions including click chemistry (e.g., cycloaddition between an azide and an alkyne to provide a 1,2,3-triazolo-linker group), and so forth.
- substitution reactions such as esterification (reaction between a hydroxyl group and a carboxylic acid derivative to provide an ester linker group), additional reactions including click chemistry (e.g., cycloaddition between an azi
- the hydroxyl groups can be used as nucleophiles directly or converted to alkoxy anions using strong bases to increase the reactivity. In each case, the hydroxy groups are transformed by the addition of the reactive electrophiles (X) in the compound X—R 1 .
- the present dendritic macromolecules can be at least a second-generation (G2) dendrimer or hyper-branched polymer, and include at least 16 end groups.
- the present dendritic macromolecules can be at least a third-generation (or pseudo-generation) (G3) dendrimer or hyper-branched polymer, and include at least 32 end groups.
- n can be 16 (G2), 32 (G3), 64 (G4), 128 (G5), 256 (G6), 512 (G7), or 1024 (G8).
- n can be 12 (G2), 24 (G3), 48 (G4), 96 (G5), and so forth.
- the irregular branching pattern can lead to slight variations from the theoretical number of end groups.
- the present dendritic macromolecules can have a molecular weight (or average molecular weight) between about 1,000 and about 1,000,000 Da.
- the dendritic macromolecules can be mobilized in a liquid medium to provide a composition for forming a dielectric material (which can be referred herein as a “dielectric composition”).
- the composition can be a solution, a dispersion, a suspension, an emulsion, or a gel, although in most embodiments, the composition is a solution or a dispersion suitable for solution-phase processes.
- the liquid medium can include solid and/or gaseous components, and that the liquid medium can be in a vapor or gaseous form.
- the term “liquid medium” can include a vaporized liquid medium.
- the term “mobilized in a liquid medium” broadly means that the designated liquid medium causes a designated solid to take on properties of a liquid or vapor.
- the solid can be dissolved in the liquid medium to form a single-phase solution, or the solid can be dispersed in the liquid medium to form a two-phase dispersion.
- the solid and the liquid medium can be combined together to form an emulsion, a suspension, a gel, or even micelles.
- solution means that a substantial proportion of a designated solute has formed a single phase with a designated solvent, but a substantial solid, liquid and/or gaseous second phase that can include dispersed particulate matter also can be present.
- the present dendritic macromolecules can have satisfactory solubility in various common organic solvents to afford a composition for forming a dielectric material via solution-phase processes.
- the present dendritic macromolecules can have satisfactory solubility in organic solvents that are orthogonal to those solvents (e.g., aromatic or polar chlorinated solvents) typically used to process common organic semiconducting molecules or polymers.
- organic solvents examples include alcohol solvents such as methanol, ethanol, isopropanol, 1-butanol, 2-ethoxymethanol, 3-methoxypropanol, cyclopentanol, cyclohexanol, and heptanol; ketone solvents such as acetone, acetylacetone, methyl ethyl ketone, methyl isobutyl ketone, 2-pentanone, 3-pentanone, 2-heptanone, 3-heptanone, cyclopentanone, and cyclohexanone; ester solvents such as ethyl acetate, propyl acetate, butyl acetate, isobutyl acetate, pentyl acetate, cyclohexyl acetate, heptyl acetate, ethyl propionate, propyl propionate, butyl propionate, butyl propionate,
- solubility characteristics of the present dendritic macromolecules therefore, can allow the fabrication of a device that includes a solution-processed dielectric material and a solution-processed organic semiconductor material, with the use of orthogonal solvents.
- solution-processable or “solution-processed” refers to the ability of a compound, for example, the present dendritic macromolecules, to be processed via various solution-phase processes including spin-coating, printing (e.g., inkjet printing, screen printing, pad printing, offset printing, gravure printing, flexographic printing, lithographic printing, mass-printing and the like), spray coating, electrospray coating, drop casting, dip coating, and blade coating.
- printing e.g., inkjet printing, screen printing, pad printing, offset printing, gravure printing, flexographic printing, lithographic printing, mass-printing and the like
- spray coating e.g., inkjet printing, screen printing, pad printing, offset printing, gravure printing, flexographic printing, lithographic printing, mass-printing and the like
- electrospray coating e.g., electrospray coating, drop casting, dip coating, and blade coating.
- the dielectric composition (and the resulting dielectric material) can include other components that can be used to selectively modify one or more properties (e.g., viscosity, dielectric properties, thermal stability, glass transition temperature) of the dielectric material to be formed.
- properties e.g., viscosity, dielectric properties, thermal stability, glass transition temperature
- the dielectric composition according to the present teachings can include inorganic materials such as SiO 2 and/or one or more high-k inorganic materials.
- Examples include BaTiO 3 , PbTiO 3 , PbZrO 3 , Pb(Ti,Zr)O 3 , Pb(Mn,Nb)O 3 , SrTiO 3 , CaTiO 3 , and MgTiO 3 .
- the dielectric composition according to the present teachings can include one or more linear dielectric polymers.
- the one or more linear dielectric polymers can be selected from fluorinated para-xylene, fluoropolyarylether, fluorinated polyimide, polystyrene, poly( ⁇ -methyl styrene), poly( ⁇ -vinylnaphthalene), poly(vinyltoluene), polyethylene, cis-polybutadiene, polypropylene, polyisoprene, poly(4-methyl-1-pentene), poly(tetrafluorethylene), poly(chlorotrifluoroethylene), poly(2-methyl-1,3-butadiene), poly(p-xylylene), poly( ⁇ - ⁇ - ⁇ ′- ⁇ ′-tetrafluoro-p-xylylene), poly[1,1-(2-methyl propane) bis(4-phenyl) carbonate], poly(cyclohexyl methacrylate), poly(4-
- perfluoro(1-butenyl vinyl ether) homocyclopolymers for example, those under the trade name CYTOP®
- fluorinated cyclopolymers include those having one of the following structures:
- the one or more linear dielectric polymers also are soluble in a solvent which does not mobilize (i.e., dissolve, delaminate, swell, or otherwise physically disturb) or adversely affect the semiconducting properties of an underlying organic semiconductor material when the composition is deposited thereon to provide a dielectric material in contact with the semiconductor material.
- the dielectric composition includes either one or more linear dielectric polymers and/or one or more inorganic dielectric materials
- the resulting dielectric material can be described as a blend dielectric material.
- a compound can be considered soluble in a solvent when at least 1 mg of the compound can be dissolved in 1 mL of the solvent.
- the dielectric composition according to the present teachings can include a silane crosslinker having the formula: (X) 3-m (Y) m Si(Z)Si(Y′) m′ (X′) 3-m′ , where Z can be selected from —O—, —(CH 2 ) n —, —(CF 2 ) n —, —(CH 2 CH 2 O) n —, —(CF 2 CF 2 O) n —, where n can be an integer from 1 to 20; X and X′ independently can be selected from halide, dialkylamino, alkoxy and carboxylate groups, and combinations thereof; Y and Y′ can be independently selected from H and alkyl; and m and m′ can independently range from 0-2.
- the present dielectric composition can include an acrylate crosslinker, an epoxide crosslinker, and/or a thiol crosslinker Examples include the following:
- the dielectric material formed from the dielectric composition can be a crosslinked matrix with improved physical and/or electronic properties.
- the crosslinked dielectric material can have an increased glass transition temperature (T g ), which can lead to enhanced thermal stability, smoother interface with an adjacent material (e.g., a semiconductor material), and/or reduced leakage current density.
- the composition can further include one or more additives independently selected from viscosity modulators, detergents, dispersants, binding agents, compatiblizing agents, curing agents, initiators, humectants, antifoaming agents, wetting agents, pH modifiers, biocides, and bactereriostats.
- additives independently selected from viscosity modulators, detergents, dispersants, binding agents, compatiblizing agents, curing agents, initiators, humectants, antifoaming agents, wetting agents, pH modifiers, biocides, and bactereriostats.
- surfactants and/or polymers e.g., polystyrene, polyethylene, poly-alpha-methylstyrene, polyisobutene, polypropylene, polymethylmethacrylate, and the like
- a dispersant e.g., polystyrene, polyethylene, poly-alpha-methylstyrene, polyisobutene,
- the composition can be deposited on a substrate via various deposition methods known in the art.
- the substrate can be an electrically conductive material (e.g., a gate electrode in a transistor, an electrode in a capacitor) or a semiconductor material (the charge carrying layer in a transistor).
- the dielectric composition is deposited on the substrate via a solution-phase process.
- the depositing step can be carried out by printing, including inkjet printing and various contact printing techniques (e.g., screen-printing, gravure printing, offset printing, pad printing, lithographic printing, flexographic printing, and microcontact printing).
- the depositing step can be carried out by spin coating, drop-casting, zone casting, dip coating, blade coating, or spraying.
- Spin-coating involves applying an excess amount of the coating solution onto a substrate, then rotating the substrate at high speed to spread the fluid by centrifugal force.
- the thickness of the resulting dielectric film prepared by this technique is dependent on the spin-coating rate, the concentration of the solution, as well as the solvent used.
- Printing can be performed, for example, with a rotogravure printing press, a flexo printing press, pad printing, screen printing or an inkjet printer.
- the thickness of the dielectric film as processed by these printing methods can be dependent on the concentration of the solution, the choice of solvent, and the number of printing repetitions.
- Ambient conditions such as temperature, pressure, and humidity, can also affect the resulting thickness of the film.
- printing quality can be affected by different parameters including, but not limited to, rheological properties of the formulations such as tension energy and viscosity.
- Dielectric materials according to the present teachings can take various forms including a wafer, a layer, a sheet, or an elongated web.
- the present dielectric materials can be monolithic (e.g., composed of a single layer) or can have multiple sublayers (i.e., in the form of a multi-layer laminate), where the multiple sublayers can have identical or different chemical compositions.
- Multilayer dielectric materials according to the present teachings have two or more layers of dielectric materials sequentially deposited on top of each other (although one or more interlayers can be present), where at least one of the layers is prepared from a composition including a dendritic macromolecule according to the present teachings.
- the multi-layer laminate can include at least one layer prepared from a composition including the present dendritic macromolecules alone in a liquid medium, and at least one layer prepared from a linear dielectric polymer or an inorganic dielectric material.
- an interlayer can be present to improve adhesion between the sublayers.
- the multi-layer laminate can include at least one layer prepared from a composition including the present dendritic macromolecules in a liquid medium along with a metal oxide, a linear dielectric polymer, a silane crosslinker, and/or an acrylate crosslinker, and at least one layer prepared from a linear dielectric polymer or an inorganic dielectric material, or at least one layer prepared from a composition including the present dendritic macromolecules alone in a liquid medium.
- a dielectric material according to the present teachings can be prepared by dissolving one or more dendritic macromolecules described herein in an organic solvent to provide a dielectric composition, and depositing (e.g., by spin-coating or printing) the dielectric composition onto a substrate to form a dielectric material.
- one or more metal oxides can be added to the dielectric composition prior to the depositing step.
- one or more linear dielectric polymers can be added to the dielectric composition prior to the depositing step.
- one or more crosslinkers can be added to the dielectric composition prior to the depositing step.
- a multi-layer dielectric material can be prepared by dissolving one or more dendritic macromolecules described herein in an organic solvent to provide a dielectric composition, where the dielectric composition optionally can include at least one of a linear dielectric polymer, a metal oxide, and a crosslinker; depositing (e.g., by spin-coating or printing) the dielectric composition onto a substrate to form a first layer; and depositing a composition that includes a linear dielectric polymer or a metal oxide to form a second layer.
- a curing step can be performed, e.g., by heating, to accelerate removal of the solvent, and/or to induce photo or thermal crosslinking.
- an irradiating step can be performed as described herein.
- an irradiating step can be performed as described herein.
- heating steps carried out at different temperatures can be performed as described herein.
- the present dendritic macromolecules can have a dielectric constant above about 2.5, preferably above about 3, wherein the dielectric constant can be determined using any procedures known in the art, including the procedures described in the standard test method ASTM D150.
- Dielectric materials of the present teachings can have large k values as measured from standard MIS and MIM capacitor structures measuring k versus voltage (V) and k versus frequency (f).
- dielectric materials of the present teachings can have a dielectric constant k greater than about 2.5, a dielectric constant k greater than about 3, a dielectric constant k of about 4 or higher, or a dielectric constant k of about 5 or higher.
- the use of a relatively high-k (k>2.5) dielectric layer will increase the capacitance of the gate dielectric. This characteristic is important because in TFT applications, a higher dielectric constant allows a larger number of mobile carriers to be induced at lower voltages. Furthermore, if the dielectric constant of a dielectric material is large, a large capacitance can be obtained for thicker dielectric films, thus reducing the leakage current.
- the dielectric compositions disclosed herein due to the end group functionalization of the dendritic macromolecules, have solubility properties that are favorable to device fabrication using solution-phase processes. The end groups also reduce the force between the mobile charge in the semiconductor and the dipole (polarization) of the high-k dendritic core. This can lead to higher mobilities in a transistor device.
- Dendritic macromolecules of the present teachings can have tuned glass transition temperature (T g ).
- T g glass transition temperature
- the present dendritic macromolecules can have a T g between about ⁇ 40° C. and about 200° C.
- Higher T g can be obtained with end group functionalization that includes rigid cyclic groups, for example, caged hydrocarbons such as adamantine, or by post-deposition crosslinking of crosslinkable end groups.
- compositions (formulations) including one or more dendritic macromolecules of the present teachings can be used to prepare single- or multi-layer dielectric materials that can exhibit a wide range of desirable properties and characteristics including, but not limited to, high dielectric constant, low leakage current densities, high breakdown voltages, low hysteresis, tuned capacitance values, uniform film thickness, solution-processability, fabricability at low temperatures and/or atmospheric pressures, air and moisture stability, and/or compatibility with diverse gate materials and/or semiconductors.
- Leakage current density typically is defined as a vector whose magnitude is the leakage current per cross-sectional area.
- leakage current refers to uncontrolled (“parasitic”) current flowing across region(s) of a semiconductor structure or device in which no current should be flowing, for example, current flowing across the gate dielectric in a thin-film transistor device.
- the leakage current density of a dielectric material can be determined by fabricating a standard metal-insulator-semiconductor (MIS) and/or metal-insulator-metal (MIM) capacitor structures with the dielectric material, then measuring the leakage current, and dividing the measured current by the area of the metal electrodes.
- MIS metal-insulator-semiconductor
- MIM metal-insulator-metal
- Dielectric materials that incorporate one or more dendritic macromolecules of the present teachings can have very low leakage current densities as measured from standard MIS and MIM capacitor structures.
- Dielectric materials prepared from dendritic macromolecules of the present teachings also can withstand very high breakdown voltages (i.e., the maximum voltage difference that can be applied across the dielectric before it breaks down and begins to conduct).
- dielectric materials of the present teachings can withstand a breakdown voltage of 4 MV/cm or higher, a breakdown voltage of 6 MV/cm or higher, or a breakdown voltage of 7 MV/cm or higher.
- the present teachings further provide articles of manufacture, for example, composites, that includes a dielectric material of the present teachings.
- the articles of manufacture can be an electronic, optical, or optoelectronic device that includes a semiconductor component, where the dielectric material of the present teachings is in contact with the semiconductor component.
- the semiconductor component can be selected from, but is not limited to, various fused heterocycles, aromatic hydrocarbons, polythiophenes, fused (hetero)aromatics (e.g., perylene imide and naphthalene imide small molecule or polymers), and other such organic semiconductor compounds or materials, whether p-type or n-type, otherwise known or found useful in the art.
- the semiconductor component can be prepared from one or more compounds and/or polymers as described in U.S. Pat. Nos. 6,585,914, 6,608,323, 6,991,749, 7,374702, 7,528,176, 7,569,693, and 7,605,225; U.S. Patent Publication Nos. 2005/0176970, 2006/0186401, 2007/0282094, 2008/0021220, 2008/0167435, 2008/0177073, 2008/0185555, 2008/0185577, 2008/0249309, and 2009/0036643; and International Publication Nos.
- the semiconductor component also can include inorganic semiconductor materials such as silicon, germanium, gallium arsenide, metal oxides, and the like.
- the articles of manufacture can an electronic, optical, or optoelectronic device that includes an electrically conductive material.
- An example is a capacitor, where the dielectric material is disposed between two electrically conductive layers.
- Another example is a transistor, where one side of the dielectric material is in contact with a semiconductor component and an opposite side of the dielectric material is in contact with an electrically conductive material (the gate electrode).
- the articles of manufacture can include a substrate.
- the substrate can be composed of a material selected from, for example, doped silicon, an indium tin oxide (ITO), ITO-coated glass, ITO-coated polyimide or other plastics, aluminum or other metals alone or coated on a polymer or other substrate, a doped polythiophene, and the like.
- ITO indium tin oxide
- ITO-coated glass ITO-coated polyimide or other plastics
- aluminum or other metals alone or coated on a polymer or other substrate aluminum or other metals alone or coated on a polymer or other substrate
- a doped polythiophene and the like.
- the transistor device also includes a source electrode and a drain electrode.
- the source and drain electrodes can be made using various deposition techniques.
- the source and drain electrodes can be deposited through a mask, or can be deposited then etched. Suitable deposition techniques include electrodeposition, vaporization, sputtering, electroplating, coating, laser ablation and offset printing, from metal or metal alloy including copper, aluminum, gold, silver, platinum, palladium, and/or nickel, or an electrically conductive polymer such as polyethylenethioxythiophene (“PEDOT”).
- PEDOT polyethylenethioxythiophene
- An aspect of the present teachings relates to a thin film transistor device including a dielectric layer comprising a dielectric material as described herein, a semiconductor layer, a gate electrode, a source electrode, and a drain electrode.
- the dielectric layer typically is disposed between the semiconductor layer and the gate electrode.
- the source and drain electrodes can be disposed above the semiconductor layer (top-contact), or the semiconductor layer can be disposed above the source and drain electrodes (bottom-contact).
- FIG. 9 illustrates the four common types of OFET structures: (a) bottom-gate top-contact structure, (b) bottom-gate bottom-contact structure, (c) top-gate bottom-contact structure, and (d) top-gate top-contact structure. As shown in FIG.
- an OFET can include a dielectric layer (e.g., shown as 8 , 8 ′, 8 ′′, and 8 ′′′ in FIGS. 9 a , 9 b , 9 c , and 9 d , respectively), a semiconductor/channel layer (e.g., shown as 6 , 6 ′, 6 ′′, and 6 ′′′ in FIGS. 9 a , 9 b , 9 c , and 9 d , respectively), a gate contact (e.g., shown as 10 , 10 ′, 10 ′′, and 10 ′′′ in FIGS.
- a dielectric layer e.g., shown as 8 , 8 ′, 8 ′′, and 8 ′′′ in FIGS. 9 a , 9 b , 9 c , and 9 d , respectively
- a semiconductor/channel layer e.g., shown as 6 , 6 ′, 6 ′′, and 6 ′′′ in FIGS.
- the method can include depositing a dielectric composition according to the present teachings onto a substrate (gate) to form a dielectric layer, wherein the dielectric composition includes one or more dendritic macromolecules described herein dissolved in a first solvent; depositing a semiconducting composition onto the dielectric layer to form a semiconductor layer, where the semiconducting composition includes one or more semiconducting compounds (e.g., small molecule compounds or polymers) dissolved in a second solvent, and where the first solvent and the second solvent are orthogonal solvents; and forming a first electrical contact and a second electrical contact (source and drain) on the semiconductor layer, thereby providing a top-contact bottom-gate organic field effect transistor.
- the method can include curing the dielectric layer, for example, by heating and/or exposure to radiation to induce crosslinking.
- the method can include depositing a dielectric composition according to the present teachings onto a substrate (gate) to form a dielectric layer, wherein the dielectric composition includes one or more dendritic macromolecules described herein dissolved in a first solvent; forming a first electrical contact and a second electrical contact (source and drain) above the dielectric material, and depositing a semiconducting composition above the first and second electrical contacts and the dielectric layer (i.e., to cover the electrical contacts and an area of the dielectric material between the electrical contacts) to form a semiconductor layer, where the semiconducting composition includes one or more semiconducting compounds (e.g., small molecule compounds or polymers) dissolved in a second solvent, and where the first solvent and the second solvent are orthogonal solvents; to provide a bottom-contact bottom-gate organic field effect transistor.
- the method can include curing the dielectric layer, for example, by heating and/or exposure to radiation to induce crosslinking.
- the method can include forming a first electrical contact and a second electrical contact (source and drain) on a substrate, depositing a semiconducting composition above the first and second electrical contacts (i.e., to cover the electrical contacts and an area of the substrate between the electrical contacts) to form a semiconductor layer, where the semiconducting composition includes one or more semiconducting compounds (e.g., small molecule compounds or polymers) dissolved in a first solvent; depositing a dielectric composition according to the present teachings above the semiconductor layer to form a dielectric layer, where the dielectric composition includes one or more dendritic macromolecules described herein dissolved in a second solvent, and where the first solvent and the second solvent are orthogonal solvents; and forming a third electrical contact (gate) above the dielectric material, wherein the third electrical contact is above an area between the first and second electrical contacts, to provide a bottom-contact top-gate organic field effect transistor.
- the method can include curing the dielectric layer, for example, by heating and/or exposure to radiation
- the method can include depositing a semiconducting composition on a substrate to form a semiconductor layer, where the semiconducting composition includes one or more semiconducting compounds (e.g., small molecule compounds or polymers) dissolved in a first solvent; forming a first electrical contact and a second electrical contact (source and drain) above the semiconductor layer; depositing a dielectric composition according to the present teachings above the first and second electrical contacts and an area of the semiconductor layer between the first and second electrical contacts to form a dielectric layer, where the dielectric composition includes one or more dendritic macromolecules described herein dissolved in a second solvent, and where the first solvent and the second solvent are orthogonal solvents; and forming a third electrical contact (gate) above the dielectric material, wherein the third electrical contact is above an area between the first and second electrical contacts, to provide a top-contact top-gate organic field effect transistor.
- the method can include curing the dielectric layer, for example, by heating and/or exposure to radiation to induce crosslinking.
- the semiconductor layer and the various electrical contacts can be formed by various deposition processes known to those skilled in the art.
- the semiconductor layer can be formed by processes such as, but not limited to, physical vapor deposition, different types of printing techniques (e.g., flexo printing, litho printing, gravure printing, ink-jetting, pad printing, and so forth), drop casting, dip coating, doctor blading, roll coating, and spin-coating.
- Electrical contacts can be formed by processes such as, but not limited to, thermal evaporation and radiofrequency or e-beam sputtering, as well as various deposition processes, including but not limited to those described immediately above (e.g., flexo printing, litho printing, gravure printing, ink-jetting, pad printing, screen printing, drop casting, dip coating, doctor blading, roll coating, and spin-coating).
- processes such as, but not limited to, thermal evaporation and radiofrequency or e-beam sputtering, as well as various deposition processes, including but not limited to those described immediately above (e.g., flexo printing, litho printing, gravure printing, ink-jetting, pad printing, screen printing, drop casting, dip coating, doctor blading, roll coating, and spin-coating).
- dendritic macromolecules and dielectric materials were prepared and characterized by NMR, differential scanning calorimetry (DSC), AFM, and metal-insulator-semiconductor (MIS) device leakage and impedance spectroscopy measurements, to demonstrate, among other things, their dielectric properties and their compatibility with various p-type and n-type organic semiconductors.
- Organic electronic devices for example, organic thin film transistors (OTFTs), specifically, organic field effect transistors (OFETs), based on these dielectric films also have been fabricated and characterized, data of which are provided below.
- D-(OH) 64 (0.59 g, 0.081 mmol) and DMAP (15.1 mg) were dissolved in dry pyridine (1.5 mL).
- the reaction mixture was allowed to stir at room temperature under nitrogen for 15 hours.
- Acetic anhydride (1 mL) was then added, and the mixture was stirred for additional 2 hours, before it was precipitated in methanol.
- the isolated solid product was washed twice with ammonia aqueous solution, and washed with methanol, leading to a white solid as the product (450 mg).
- D-(OH) 64 (0.60 g, 0.082 mmol) and DMAP (15.2 mg) were dissolved in dry pyridine (1.5 mL).
- the reaction mixture was allowed to stir at room temperature under nitrogen for 14 hours.
- Acetic anhydride (1 mL) was then added, and the mixture was stirred for additional 2 hours, before it was precipitated in methanol.
- the isolated solid product was washed twice with ammonia aqueous solution, then dissolved in DCM, and passed through a syringe filter.
- D-(OH) 64 (0.59 g, 0.081 mmol) and DMAP (15.0 mg) were dissolved in dry pyridine (1.5 mL).
- a solution of dicyclohexyl acetyl chloride (0.65 g, 2.68 mmol) in dry DCM (2 mL) was added slowly, and the resulting mixture was stirred at room temperature for 3 hours.
- a solution of 2-methylhexyl carbonyl chloride (1.27 g, 7.91 mmol) in dry DCM (4 mL) was added slowly.
- the reaction mixture was allowed to stir at room temperature under nitrogen for additional 14 hours.
- Acetic anhydride (1 mL) was then added, and the mixture was stirred for additional 2 hours, before it was precipitated in methanol.
- a mixture of 6.24 g (18.9 mmol) of A-1, 3.94 g (37.9 mmol) of malonic acid, 0.24 g (2.8 mmol) of piperidine, and 10 mL of pyridine was heated in an oil bath at 100° C. for 1 hour. The mixture was heated to 130° C. for 1 hour, then cooled to room temperature. The mixture was treated with 100 mL of water and 10 mL of concentrated aqueous HCl. The mixture was extracted with 150 mL of diethyl ether. The separated ethereal layer was washed successively with 50 mL of 1.0 N aqueous HCl and 50 mL of brine.
- Dendritic macromolecule formulations were prepared by dissolving 1-150 mg of a selected dendritic macromolecule in 1 mL of solvent. The formulations were spin-coated onto clean silicon substrates at 1000-2000 rpm (acceleration 20) to give films of thicknesses in the range of about 50-650 nm. Highly n-doped silicon wafers (obtained from Montco Silicon Tech, Inc., Spring City, Pa.) were cleaned by sonication in organic solvents before use. After the spin-coating step, the films were then annealed in a vacuum oven at about 50-100° C. for about 1-10 minutes to completely remove any residual solvent.
- MIS capacitor structures were fabricated using the resulting dielectric films, and the capacitance of the dielectric films was measured.
- heavily doped n-type Si MEMC Electronic Materials, Antimony/n-doped
- an I-V scan was performed by applying bias to the traixial probe and measuring current through the circuit.
- the scan rate was between 5-15 s/step, which was controlled by setting the delay time to between 0.5 s and 2 s and the number of measurements per step between 10 and 20.
- a representative plot of leakage current density (J) versus voltage (V) is shown in FIG. 11 .
- a digital capacitance meter (Model 3000, GLK Instruments) and impedance/gain-phase analyzer (SI 1260, Solartron Analytical) were used for capacitance measurements.
- Representative plots of dielectric constant (k) versus voltage (V) and capacitance (C) vs. frequency (f) are shown in FIG. 10 .
- bottom-contact top-gate OFETs were fabricated using a dielectric material of the present teachings as the dielectric layer.
- Step 1 Substrate: Glass slides 1′′ ⁇ 1′′, 0.4 mm thickness (PGO) were cleaned by sonication in ethanol three times and kept in ethanol before the next step.
- Step 3 Step 3.
- a core-cyanated perylene semiconductor was prepared as a 7 mg/mL solution in DCB (Aldrich) and carefully heated on a 120° C. heating plate until the compound was completely dissolved. Substrates from step 2 were loaded onto the spin-coater and the semiconductor solution was applied to the substrate through a 0.2 ⁇ m PTFE syringe filter (Millipore) and was spin-coated at 1500 rpm (acceleration 20). The resulting film was baked at about 110° C. on a hot-plate before proceeding to the next step. Step 4. Gate Dielectric The dielectric layer was prepared by spin-coating a solution of dendrimer D1 or D2 at 1000 rpm (acceleration 20) for 2 minutes.
- Gate electrode The gate electrode was evaporated in the same metal evaporator mentioned about to a final thickness of about 300 ⁇ at a rate of 0.6 ⁇ /s.
- the devices were tested using a Signatone H100 series probe station equipped with Keithley Interactive Test Environment software in a 4-terminal-n-FET mode. Transfer plots were recorded with 60 V drain bias, 0 V source bias, and a gate bias sweeping from ⁇ 60 V to 60 V at 5 V intervals. Output plots were recorded with 0-60 V drain bias with 5 V steps and 0-60 V gate bias with 10 V steps, source bias at 0V. Transfer plots of such top-gate devices are shown in FIG. 12 .
- Pentacene OFETs were fabricated with dielectric films on silicon gate materials.
- a Si wafer (Montco) was prepared as 1′′ ⁇ 1′′ pieces and cleaned by sonication with THF and ethanol. The wafers were loaded on a spin-coater and rinsed with methanol twice at 5000 rpm.
- a solution of the macromolecule of the present teachings e.g., D1, D2, a D1+PMMA blend
- the films were baked at about 110° C. in a vacuum oven for about 20 minutes.
- Pentacene Sigma-Aldrich, St.
- Device Carrier mobility Structure Dielectric Semiconductor ⁇ cat (cm 2 /Vs) I on /I off Top-gate, D1 PDI1MP-CN2 1-2 10 4 ⁇ 10 5 bottom- contact Top-gate, D2 PDI1MP-CN2 0.5-2 10 4 ⁇ 10 5 bottom- contact Top-gate, D4 PDI1MP-CN2 0.5-1 10 4 ⁇ 10 5 bottom- contact Top-gate, D5 PDI1MP-CN2 0.5-1 10 4 ⁇ 10 5 bottom- contact Bottom- D1 Pentacene 0.1-0.5 10 5 ⁇ 10 6 gate, top- contact Bottom- D1 + PMMA Pentacene 0.1-0.5 10 5 ⁇ 10 6 gate, top- contact
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Abstract
Description
where T is O, S, NH, N-alkyl, N-aryl, N-(arylalkyl) (e.g., N-benzyl), SiH2, SiH(alkyl), Si(alkyl)2, SiH(arylalkyl), Si(arylalkyl)2, or Si(alkyl)(arylalkyl). Examples of such heteroaryl rings include pyrrolyl, furyl, thienyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazolyl, tetrazolyl, pyrazolyl, imidazolyl, isothiazolyl, thiazolyl, thiadiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, indolyl, isoindolyl, benzofuryl, benzothienyl, quinolyl, 2-methylquinolyl, isoquinolyl, quinoxalyl, quinazolyl, benzotriazolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxadiazolyl, benzoxazolyl, cinnolinyl, 1H-indazolyl, 2H-indazolyl, indolizinyl, isobenzofuyl, naphthyridinyl, phthalazinyl, pteridinyl, purinyl, oxazolopyridinyl, thiazolopyridinyl, imidazopyridinyl, furopyridinyl, thienopyridinyl, pyridopyrimidinyl, pyridopyrazinyl, pyridopyridazinyl, thienothiazolyl, thienoxazolyl, thienoimidazolyl groups, and the like. Further examples of heteroaryl groups include 4,5,6,7-tetrahydroindolyl, tetrahydroquinolinyl, benzothienopyridinyl, benzofuropyridinyl groups, and the like. In some embodiments, heteroaryl groups can be substituted as described herein.
D-(L-R1)n
wherein:
D is the residue of a dendrimer or hyperbranched polymer;
L is a covalent bond or a linker group;
R1 is an organic group comprising one, two, three or four 3-40 membered optionally substituted cyclic groups; and
n is an integer in the range of 12-1024.
(X)3-m(Y)mSi(Z)Si(Y′)m′(X′)3-m′,
where Z can be selected from —O—, —(CH2)n—, —(CF2)n—, —(CH2CH2O)n—, —(CF2CF2O)n—, where n can be an integer from 1 to 20; X and X′ independently can be selected from halide, dialkylamino, alkoxy and carboxylate groups, and combinations thereof; Y and Y′ can be independently selected from H and alkyl; and m and m′ can independently range from 0-2.
TABLE 1 |
Performance of devices fabricated using |
dielectrics of the present teachings. |
Device | Carrier mobility | |||
Structure | Dielectric | Semiconductor | μcat (cm2/Vs) | Ion/Ioff |
Top-gate, | D1 | PDI1MP-CN2 | 1-2 | 104−105 |
bottom- | ||||
contact | ||||
Top-gate, | D2 | PDI1MP-CN2 | 0.5-2 | 104−105 |
bottom- | ||||
contact | ||||
Top-gate, | D4 | PDI1MP-CN2 | 0.5-1 | 104−105 |
bottom- | ||||
contact | ||||
Top-gate, | D5 | PDI1MP-CN2 | 0.5-1 | 104−105 |
bottom- | ||||
contact | ||||
Bottom- | D1 | Pentacene | 0.1-0.5 | 105−106 |
gate, | ||||
top- | ||||
contact | ||||
Bottom- | D1 + PMMA | Pentacene | 0.1-0.5 | 105−106 |
gate, | ||||
top- | ||||
contact | ||||
Claims (18)
D-(L-R1)n,
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WO2011088343A2 (en) | 2011-07-21 |
WO2011088343A3 (en) | 2011-09-29 |
US20110175089A1 (en) | 2011-07-21 |
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